KR100411398B1 - 베타-디-리보푸라노즈 유도체의 제조방법 - Google Patents
베타-디-리보푸라노즈 유도체의 제조방법 Download PDFInfo
- Publication number
- KR100411398B1 KR100411398B1 KR10-2001-0076802A KR20010076802A KR100411398B1 KR 100411398 B1 KR100411398 B1 KR 100411398B1 KR 20010076802 A KR20010076802 A KR 20010076802A KR 100411398 B1 KR100411398 B1 KR 100411398B1
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- triazole
- mole
- ribofuranosyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 9
- HMFHBZSHGGEWLO-TXICZTDVSA-N beta-D-ribose Chemical class OC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-TXICZTDVSA-N 0.000 title 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229940092714 benzenesulfonic acid Drugs 0.000 claims abstract description 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000002425 crystallisation Methods 0.000 claims description 22
- 230000008025 crystallization Effects 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 4
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 abstract description 12
- 229960000329 ribavirin Drugs 0.000 abstract description 12
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 abstract description 12
- 230000000840 anti-viral effect Effects 0.000 abstract description 4
- QMPFMODFBNEYJH-UHFFFAOYSA-N methyl 1h-1,2,4-triazole-5-carboxylate Chemical compound COC(=O)C1=NC=NN1 QMPFMODFBNEYJH-UHFFFAOYSA-N 0.000 description 15
- ZRCNJIAXPDPHRD-FDYHWXHSSA-N [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(1,2,4-triazol-1-yl)oxolan-2-yl]methyl acetate Chemical compound C(C)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C)=O)COC(C)=O)N1N=CN=C1 ZRCNJIAXPDPHRD-FDYHWXHSSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ZEWJFUNFEABPGL-UHFFFAOYSA-N 1,2,4-triazole-3-carboxamide Chemical compound NC(=O)C=1N=CNN=1 ZEWJFUNFEABPGL-UHFFFAOYSA-N 0.000 description 1
- -1 2,3,5-tri-O-acetyl-β-D-ribofuranosyl Chemical group 0.000 description 1
- AOTIOYWDKQYVFY-ZGFBMJKBSA-N C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O)N1N=CN=C1 Chemical compound C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O)N1N=CN=C1 AOTIOYWDKQYVFY-ZGFBMJKBSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- GCZABPLTDYVJMP-CBUXHAPBSA-N [(2r,3r,4r,5s)-5-acetyloxy-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H]1OC(=O)C=1C=CC=CC=1)OC(=O)C=1C=CC=CC=1)OC(=O)C)OC(=O)C1=CC=CC=C1 GCZABPLTDYVJMP-CBUXHAPBSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- DHZYWCBUDKTLGD-UHFFFAOYSA-N ethyl 1h-1,2,4-triazole-5-carboxylate Chemical compound CCOC(=O)C1=NC=NN1 DHZYWCBUDKTLGD-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/056—Triazole or tetrazole radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2001-0076802A KR100411398B1 (ko) | 2001-12-06 | 2001-12-06 | 베타-디-리보푸라노즈 유도체의 제조방법 |
| EP02791004A EP1451178A4 (de) | 2001-12-06 | 2002-11-30 | Verfahren zur herstellung von beat-d-ribofuranosederivaten |
| PCT/KR2002/002254 WO2003048157A1 (en) | 2001-12-06 | 2002-11-30 | Processes for preparing ¥â-d-ribofuranose derivatives |
| AU2002365852A AU2002365852A1 (en) | 2001-12-06 | 2002-11-30 | Processes for preparing %a-d-ribofuranose derivatives |
| US10/310,887 US6660854B2 (en) | 2001-12-06 | 2002-12-06 | Processes for preparing β-D-ribofuranose derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2001-0076802A KR100411398B1 (ko) | 2001-12-06 | 2001-12-06 | 베타-디-리보푸라노즈 유도체의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20030046609A KR20030046609A (ko) | 2003-06-18 |
| KR100411398B1 true KR100411398B1 (ko) | 2003-12-18 |
Family
ID=19716692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2001-0076802A KR100411398B1 (ko) | 2001-12-06 | 2001-12-06 | 베타-디-리보푸라노즈 유도체의 제조방법 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6660854B2 (de) |
| EP (1) | EP1451178A4 (de) |
| KR (1) | KR100411398B1 (de) |
| AU (1) | AU2002365852A1 (de) |
| WO (1) | WO2003048157A1 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003253380A1 (en) * | 2002-08-12 | 2004-03-11 | F. Hoffmann-La-Roche Ag | Process for producing a ribofuranose |
| CN101397316B (zh) * | 2008-10-23 | 2012-05-23 | 浙江工业大学 | 一种利巴韦林缩合物的化学合成方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55160793A (en) * | 1979-05-29 | 1980-12-13 | Microbial Chem Res Found | Preparation of virazole |
| JPS6075492A (ja) * | 1983-10-03 | 1985-04-27 | Takeda Chem Ind Ltd | シチジン誘導体の製造法 |
| WO1998016186A2 (en) * | 1996-10-16 | 1998-04-23 | Icn Pharmaceuticals, Inc. | Monocyclic l-nucleosides, analogs and uses thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3798209A (en) | 1971-06-01 | 1974-03-19 | Icn Pharmaceuticals | 1,2,4-triazole nucleosides |
| JPS4980070A (de) * | 1972-12-05 | 1974-08-02 |
-
2001
- 2001-12-06 KR KR10-2001-0076802A patent/KR100411398B1/ko active IP Right Grant
-
2002
- 2002-11-30 AU AU2002365852A patent/AU2002365852A1/en not_active Abandoned
- 2002-11-30 EP EP02791004A patent/EP1451178A4/de not_active Withdrawn
- 2002-11-30 WO PCT/KR2002/002254 patent/WO2003048157A1/en not_active Application Discontinuation
- 2002-12-06 US US10/310,887 patent/US6660854B2/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55160793A (en) * | 1979-05-29 | 1980-12-13 | Microbial Chem Res Found | Preparation of virazole |
| JPS6075492A (ja) * | 1983-10-03 | 1985-04-27 | Takeda Chem Ind Ltd | シチジン誘導体の製造法 |
| WO1998016186A2 (en) * | 1996-10-16 | 1998-04-23 | Icn Pharmaceuticals, Inc. | Monocyclic l-nucleosides, analogs and uses thereof |
Non-Patent Citations (1)
| Title |
|---|
| J Med Chem,Vol 43, p1019-1028,2000 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1451178A1 (de) | 2004-09-01 |
| US6660854B2 (en) | 2003-12-09 |
| WO2003048157A1 (en) | 2003-06-12 |
| KR20030046609A (ko) | 2003-06-18 |
| AU2002365852A1 (en) | 2003-06-17 |
| EP1451178A4 (de) | 2006-10-04 |
| US20030120064A1 (en) | 2003-06-26 |
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